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| | (1-Methyl-1H-pyrazol-5-yl)-boronic acid Basic information |
| Product Name: | (1-Methyl-1H-pyrazol-5-yl)-boronic acid | | Synonyms: | (2-methyl-3-pyrazolyl)boronic acid;(1-Methyl-1H-pyrazol-5-yl)-boronic acid;Boronic acid, B-(1-methyl-1H-pyrazol-5-yl)-;(1-Methyl-1H-pyrazol-5-yl...;1-Methyl-pyrazole-5-boronic acid;(1-methyl-1H-pyrazol-5-yl)boronic acid(SALTDATA: FREE);1-Methyl-1H-pyrazole-5-boronic acid;1-Methyl-1H-pyrazol-5-yl-5-boronic acid | | CAS: | 720702-41-0 | | MF: | C4H7BN2O2 | | MW: | 125.92 | | EINECS: | | | Product Categories: | | | Mol File: | 720702-41-0.mol |  |
| | (1-Methyl-1H-pyrazol-5-yl)-boronic acid Chemical Properties |
| Boiling point | 323.0±34.0 °C(Predicted) | | density | 1.23±0.1 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Store in freezer, under -20°C | | pka | 8.00±0.58(Predicted) | | Appearance | White to off-white Solid | | InChI | InChI=1S/C4H7BN2O2/c1-7-4(5(8)9)2-3-6-7/h2-3,8-9H,1H3 | | InChIKey | MGNBKNBEZGLHNF-UHFFFAOYSA-N | | SMILES | B(C1N(C)N=CC=1)(O)O |
| Risk Statements | 36 | | Safety Statements | 26 | | HS Code | 2933199090 |
| | (1-Methyl-1H-pyrazol-5-yl)-boronic acid Usage And Synthesis |
| Uses | 1-Methyl-1H-pyrazole-5-boronic Acid acts as a reagent for the design, synthesis and evaluation of novel porcupine inhibitors featuring a fused 3-ring system based on ‘reversed’ amide scaffold. | | Synthesis | General procedure for the synthesis of 1-methyl-1H-pyrazole-5-boronic acid from 1-methylpyrazole: 1-methylpyrazole (25 mL, 0.3 mol) was dissolved in 500 mL of tetrahydrofuran (THF). The solution was then cooled to -78°C in a dry ice/isopropanol bath. After the solution temperature stabilized at -78 °C, n-butyllithium (n-BuLi, 140 mL, 0.40 mol) was slowly added dropwise through the cannula. After the dropwise addition, the reaction mixture was stirred continuously at -78 °C for 1.5 hours. Next, triisopropyl borate (280 mL, 1.2 mol) was added to the reaction system via cannula and the reaction mixture was allowed to slowly warm from -78 °C to 0 °C while stirring overnight. Upon completion of the reaction, the pH of the mixture was adjusted to 6 with 1 N hydrochloric acid (HCl).Subsequently, THF was evaporated under reduced pressure and the remaining aqueous phase was extracted with ethyl acetate (EtOAc, 2 × 100 mL). Finally, the solid was collected by filtration to afford 108 g (100% yield) of 1-methyl-1H-pyrazole-5-boronic acid as a yellow solid. | | References | [1] Patent: WO2005/12254, 2005, A1. Location in patent: Page/Page column 101
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1923 - 1936
[3] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 6, p. 931 - 939
[4] Patent: WO2004/58722, 2004, A1. Location in patent: Page 63; 62 |
| | (1-Methyl-1H-pyrazol-5-yl)-boronic acid Preparation Products And Raw materials |
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